


Cabana Boy

by GremlinGirl



Category: Star Wars Sequel Trilogy
Genre: Age Difference, Alcohol, Anal Sex, Bottom!Ben, Cabana Boy!Ben, Feminization, Hour, Kylux Summer Fest 2019, Lipstick, M/M, Prostitution, Rimming, Top!hux, Watch, eating ass, kyluxxoxo, lips
Language: English
Status: Completed
Published: 2019-07-12
Updated: 2019-07-12
Packaged: 2020-06-26 23:18:33
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,813
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19778524
Author URL: https://archiveofourown.org/users/GremlinGirl/pseuds/GremlinGirl
Summary: Ben has the worst job ever working at a high end resort during his summer college courses. When an older client offers him a large sum of cash, Ben discovers a new way to make ends meet that's maybe a bit more enjoyable.





	Cabana Boy

It was potentially the worst job ever, but Ben needed the money. Summer classes at the university still cost money, and his parents had cut him off. It wasn’t fair, in his mind. Ben had done everything he was meant to do: gone to school, gotten good grades, stayed mostly out of trouble. He didn’t even drink like most twenty years old did. But they’d decided he needed to learn responsibility, so short of sending him emergency money if he ran out of food, he was on his own. 

And he’d gotten this job for the summer, at a resort club for the super rich. His family wasn’t poor by any means, but this kind of life definitely seemed excessive. He worked as a server, walking up and down beside the pool and going to each cabana to offer drinks and food. There was a small hut that had a bar set up inside, a fridge, and a grill. He worked inside the hut sometimes, but usually he was constantly walking back in forth in the six inch heels that were part of his uniform. Embarrassingly, the rest wasn’t any better. A blue skirt that barely reached mid thigh, and a halter top that hugged his wide frame. He got regular whistles from the rich clientele, but most didn’t try to flirt directly with him. 

There were a few. One man who always ordered several trays of food each night, forcing Ben to make multiple trips. Lewd comments were always made about his “busty chest” and grabbing hands had wandered a bit too far along his legs. 

That was the worst of it, though. Ben could deal with all of that. It was really the heat and the incessant boredom that really got to him. He preferred the night shift, if only because he wouldn’t be out in the sun all day. But he could only work that shift on the weekends, since he had night classes during the week. 

Saturday night, the muggy temperatures made walking around in his getup even worse. Ben carried a tray with a bottle of wine and two glasses to cabana four, and he paused outside the white curtains which were drawn shut on each side. This usually meant the patron wanted privacy, but Ben was hot, and he was tired of these spoiled, rich men making him wait. “Sir, your wine is here,” he called, then pushed the curtain aside and stepped in. Each cabana was set up with two lounge chairs, a small table for setting food and drinks on, and a large couch in the very back. Inside, Ben found the man locking lips with one of the other servers, and Ben set the wine and tray down and quickly got out of there. 

It was the worst. So many of his coworkers threw themselves at these men in hopes of catching their eyes. It was a good way to make some extra money on the side, and the clientele had come to expect it of them. Ben’s refusal to do the same was generally met with surprise. It’s not like he was going to turn anyone in. Everyone was just trying to make ends meet, but he didn’t want to debase himself. 

Going down the row of cabanas, most of which were empty as the clients had retired to their rooms in the resort hotel, Ben came to the last one in the row where a man was still sitting with the curtains pulled back. He was watching the pool, sipping on a martini from the bar, and he kept checking his watch as if he were waiting for something. “Sir? Can I get you anything else?” Ben asked, quietly. 

“Hm? No, no, I’m fine.” The client looked at him, light eyes scanning him. Ben wanted to turn around and walk back to the bar, but he found himself frozen under the man’s stare. He was in his late thirties, dressed in shorts and a tank top. He was thin, but not weak looking, and his hair was a bright red that stuck out even in the darkness. He had a heavy, silver watch that sat on his left arm, and by the look in his eyes, and the four empty glasses beside him, Ben could tell he was at least a little bit drunk. 

“Do you wanna come here, pretty thing?” 

“No. I’ll be at the bar until midnight if you need anything, sir.” Ben turned and walked away, feeling the stranger’s eyes on him the entire time. The pool was illuminated by lights along the walls, and there was a large light on the side of the building that shone on the area, bathing it in cool, white light. Ben went back into thut hut, and he sat down, picking up his phone which he’d left under the counter on top of a stack of boxes. He wasn’t going to spend the next several hours needlessly walking up and down the poolside and checking on the clients. They could come up here if they needed anything. They could stay in their cabanas all night if they wanted, as they were rented for twelve hour slots, but the bar would close at midnight, and the grill was already off and cleaned for the night. 

Ben texted his roommate, complaining how muggy and hot it was, despite the sun having set two hours ago. Be was sitting on a stool with his legs crossed, holding his hair up off of his neck, wishing there was a fan or something in here. There was the large, open window in front and the refrigeration and freezer units in the back, but they weren’t allowed anything that would chase the heat away. 

He was startled by a voice at the window. “Hey, pretty thing.” Looking up, he saw the man from before standing there, smirking at him. Ben blinked in surprise, then put his phone away, back under the counter again. Standing up, he moved close to the window with his best customer service veneer covering annoyance. Everything about being here was annoying. 

“Can I help you, sir?” 

“Are you working alone, tonight?” he asked, leaning over the window and looking Ben over curiously. 

“Yes, sir. I’m alone on the shift until midnight, which…” He reached down to check his phone again. “Is in about an hour.” 

He smiled, knowingly, then fished around in his pocket. He presented a wad of cash, and he counted out five from the top and pulled them from the stack. He slid them to the edge of the window, then winked. “Go ahead and pocket that, and I’ll see you in my cabana in one hour, then.” 

“Oh, sir, I don’t-” 

“Tick tock,” he said, holding his arm up and tapping his watch face lightly. The client walked off before Ben could say anything else. 

He reached forward with a sigh, grabbing the bills. He paused when he saw the man had counted out five hundred dollar bills. Five. Five hundred dollars. Ben’s brain short-circuited as he considered that, and he sank back down on the stool again. Surely it had been a mistake. The man should have counted out twenties or even fifties. Not this much money.” Ben quickly went and grabbed his bag from the back and he stuffed the money inside. But...no, he couldn’t do that. He pulled it out again, looking out the window toward the cabanas. 

Ben hadn’t known this was the kind of money being slung around. He went and grabbed his phone, pulling up his roommate’s number, and he pressed the call button, because he needed advice. When Poe picked up, Ben immediately started talking, barely waiting for a greeting. “So, if a man offered you five hundred bucks to suck his dick, would you do it?” he asked. 

“Uh…” Poe sounded high, not all that unusual. “Yeah, dude. Go for it.” 

“But...I mean, isn’t it kind of demeaning?” he asked, looking down at the money in his hand. He wanted to keep it so badly. 

“Five hundred bucks, dude? That could cover so much in a month. I mean, don’t quit your day job. You ain’t that pretty.” He chuckled to himself, and Ben frowned and pulled the phone away from his ear a bit. “Hey, hey, wait. In this situation, is the guy hot or, is he like, eighty?” 

Ben bit his lip, looking toward the cabana again. “He’s pretty hot. In that...older guy, Daddy kind of way, I guess.” 

“Daddy, huh? Yeah, dude. Suck his dick, and then go halfsies with me on the cash.” 

“You’re so very helpful,” Ben said, sarcastically, then hung up on Poe laughing at him. Sliding his phone into his bag, he put the money in a safe place, then went and poured himself a drink. Something he definitely wasn’t allowed to do, but it’s not like there were security cameras. No, the clients didn’t like that, so they’d been removed a month ago. It was hard to get up to seedy behavior when there was a permanent video record of it. Ben sniffed at the alcohol, turning his face away for a moment. He definitely didn't drink for a good reason, but if he was going to go blow a random client in his cabana, he definitely needed the liquid courage. 

He figured he’d decide what to do over the next hour. He wasn’t used to this kind of thing, and he’d never even fully considered doing it before. Men had propositioned him in the past, but no one had waved five hundred bucks in his face. Ben glanced up when he heard heels on the sidewalk by the pool, and he saw the other serve leaving the cabana and walking back to the bar. Coming in through the side entrance, he was throwing his hair up into a ponytail and pushing off his heels. They were given lockers, but lots of people chose to keep their bags here instead. It was a lot easier to just switch into a pair of comfortable shoes, then rush back to their cars rather than spending a lot of time in a changing room. 

“Hey,” Ben said, catching his attention. The other server looked at him like he had grown a second head or something, which was fair enough. Most of the time, they didn’t speak much to each other. It’s not like Ben made friends on the job, and no one else wanted to, either. “Hey, uh...I just wanted to ask…” 

He stood with a hand on his hip, watching Ben expectantly, an eyebrow slowly lifting. His lips were swollen and red from the illicit activities he’d gotten up to. “What?” 

“How bad is it? To sleep with these guys?” 

He blinked, surprised, then let out a loud laugh. “Oh, I thought you were trying to tell me off.” Shaking his head, the young man bent and pulled out a pair of canvas shoes, sliding them on his feet. “It’s not bad at all. Better than risking sunburn, and cleaning up trash from the pool, and walking back in forth in these heels all day. Some guys are kinda rough, but they know better than to leave bruises, and if you don’t like what they’re doing, just give ‘em a smack and get out.” 

“Right…” Ben crossed his arms, looking back over toward the cabanas again. That client would be waiting on him. Reaching over, he turned on the computer again, looking down the list of tabs to find which client was in the last cabana. Armitage Hux. Biting his lip, Ben wondered if he could really go through with this. 

“Hey, if you’re thinking about doing it, don’t get scared. You’ve fucked before, right?” 

Ben looked over, then nodded. “Uh, yeah, of course.” 

“Then there’s no difference. ‘Cept they might want you to call them sir or something.” He shrugged, then picked up his bag and swung it over his shoulder. “Okay, I got off an hour ago, so I’m heading out. You working tomorrow?” 

“Yeah, closing shift again.” 

“Cool. See you later, then.” 

The server left, and Ben went over to check his phone. Thirty more minutes. He poured himself another drink, downing this one faster than the other. The third, he sipped at, checking the time every few minutes, waiting to see anyone come out of the cabanas. He finally saw one move, but it was the client from earlier who’d ordered the drinks. He walked up, and Ben quickly hid his glass behind the computer. The man offered a card to pay his tab, and Ben completed the transaction. He was maybe moving a bit slower than he normally would, and somewhere in the back of his head, he was starting to realize that the third drink may have been a mistake. The client winked at him, then walked away, and Ben checked his phone again. Fifteen minutes. 

He finished the drink, then put the glass away to be washed later. He was supposed to do it at closing. He needed to go down and clean out the empty cabana, but he couldn’t be bothered. Getting up, he smoothed his skirt down, and pulled out his phone to check his face. He was wearing a light red lipstick, which wasn’t technically part of the uniform, but seemed to get him better tips. He sat back down to reapply it, then put his phone down and looked toward the cabana. He held his breath, seeing that Armitage Hux had walked out and was standing just outside his cabana, smoking a cigarette. The man smiled at him, then took a long drag of his cigarette. 

Ben couldn’t take it anymore. He threw his phone in his bag, then logged himself out of the computer, which would clock him out of work as well. He made sure he was steady in his tall heels before walking out of the hut and down toward the cabana. He arrived in front of the man, subtly realizing that he was a good few inches taller than him. At least in heels anyway, but this didn’t seem to change how the client was looking at him. 

“Pretty thing. Go ahead and go in, and uh...get on your knees for me.” 

“Do you want me to take my clothes off?” Ben asked, awkwardly, his cheeks a bit flushed from the alcohol he drank. 

“No. Just on your knees. I’m going to finish my cigarette.” 

Nodding, Ben turned and walked slowly through the curtain and into the cabana. He slipped between the two lounge chairs and pushed the table to the side. Bending down, he got on his knees and stared at the ground. The ground floor was hard, but it wasn’t that bad. He steadied himself with a breath, then looked up toward the curtain, waiting for it to move aside and Hux to come inside. 

Even though he was expecting it, Ben still started when Hux walked in. He looked down at Ben, smiling at him, then went to pick up a glass of wine. There was a bottle sitting on the table that he must have ordered earlier in the night. Hux took a sip, watching Ben, and he came closer and ran his fingers through his hair. “You’ve never done this before. I can see it on your face. You pretty thing. Tell me it isn’t your first time having sex?” 

“No…” Ben blinked, looking away, then he smoothed his skirt down and adjusted his top. It stopped just above his stomach, leaving his navel exposed, and there was a shiny ring glittering in his belly button. Ben wondered if this made him look like a slut and that was why Hux had approached him in the first place. “Um, what do you want me to call you?” he asked, softly. 

“Sir will work just fine.” 

Hux tipped his head back, downing his wine, then he casually pushed down his shorts. The suddenness of it had Ben leaning back, eyes wide, and Hux chuckled at him. “Cutie,” he said, setting his glass to the side. He pushed his shirt over his head, stripping himself of his sandals and shorts next. His underwear came off, and Ben kept his eyes forward, looking just past Hux’s naked body. “Don’t be shy, pretty thing. What should I call you?” 

“Ben,” he said, because he wasn’t sure what else to say. Was he supposed to come up with some sort of alias? Like a stripper? Should he go by Candy or Glitter or… His brain went blank when the tip of Hux’s cock pressed against his lips. He opened up, letting him in, and he made a soft noise at the heady taste settling on his tongue. Hux’s hips moved, and Ben could feel coarse hairs tickling his lips and chin, balls slapping against his face obscenely. He gagged softly, the tip of Hux’s cock sliding down the back of his throat. Hux held him still for a moment, moaning over him. 

It wasn’t his first blow job. But it was his second. Ben had been on his knees at a party before, sucking on some frat guy who’d promised him a ride home from a party. He supposed this was essentially like that, and he should stop thinking it wasn’t. But Hux was admittingly gentler with him, pulling back and waiting for him to catch his breath before pushing back in. However, a pace had to be set eventually, and after a few minutes of slow drags, Hux began to speed up. He was moaning loudly, hardly caring if anyone could hear them. Then again, no one else was ever really quiet, and there was no one out here anyway. Ben settled his hands on Hux’s thighs, shutting his eyes as his throat was fucked. 

Hux gripped his hair tighter, dragging Ben’s head forward. “Fuck yeah, baby. Being a good boy.” Ben’s eyes opened, and he glanced up at Hux, watching him from below as his expression shifted. “Such a pretty thing.” His words were slurred together a bit, and Ben didn’t want to question that. He scratched gently at Hux’s thighs, nostrils flaring as he tried to breathe. 

He went for a few more thrusts before pulling out, his cock falling sloppily from Ben’s lips and bringing a backlog of saliva that embarrassingly dripped down his chin. Ben quickly tried to wipe it away, his lipstick smearing. Hux was still quite hard, and he looked at him again, curiously. Hux was watching him, stroking the base of his cock. “Sir?” Ben asked, tilting his head. His voice came out rough. 

Hux bent down and patted the lounge chair. “Climb up here, Ben. Get on your knees, stick your ass out, and grab the back.” He stepped back, waiting and watching. 

Ben hadn’t thought it went further than a blowjob. He got up slowly, then got onto the chair. He pressed his legs together, then bent over and wrapped his arms around the back of the chair, grabbing at the wood paneling that was under the cushions. It was a lot nicer than kneeling on the hard ground, at the very least. 

“Good boy.” Ben felt his cheeks flushing darker at that, and his skirt was pushed up as Hux also batted at his ankles to get him to spread his legs. He placed one leg on the very end of the lounge chair, then leaned in and placed kisses along Ben’s exposed thighs. “Such a pretty boy. A big boy.” Hux smacked his thigh, and Ben made a squeaking complaint. 

“Sir,” he said, voice a bit higher than usual. 

“Shhh, calm down.” Hux kissed him, right where his hand had connected, then he moved up and hooked his fingers in the elastic band of Ben’s panties, pulling them down around his thighs and leaving them bunched around his knees. Ben flushed darkly, the light in the cabana fully exposing him for Hux to see. He felt fingers prying his cheeks apart, and Hux’s satisfied hum was all he really needed. “Pretty.” He placed a kiss directly on the pucker of Ben’s hole, and hot breath ghosted along his crack. “You wax down here,” Hux said. 

“Yes, sir,” Ben whispered, squeezing his eyes shut in embarrassment. I do around my dick, too.” 

“Good boy. Slutty boy. I like it.” Hux kissed him again, this time pressing closer, and Ben felt a tongue dart out to trace in a circle around his rim. Ben let out a soft sound as Hux’s tongue began lick at his hole, causing him to twitch in response. Hux held his cheeks apart as he swept his tongue up and down, swirling around his rim each time. Ben felt himself tingling, and he buried his face in the lounge chair’s cushion. 

Saliva began dripping through his crack, warm and slippery. It dropped down over his balls as well, and Ben’s cock began to swell in response to the constant licking. He’d never had this done before. Hux was voracious, devouring his hole, and soon his tongue was prodding into him. Hux panted, pulling back just enough to breath, and Ben shuddered and warm hair ghosted over his slobbery hole. He moaned, feeling Hux tentatively licking him again. 

“Relax for me, baby. So i can taste you.” He flattened his tongue against the rim and slowly lapped along his hole several times. Ben let out a short cry, muffled by the cushion, his cheeks flushing even darker. Hux took this as encouragement, and he speared his tongue into Ben’s hole. Finally inside, Hux pushed as deep as the muscle could go, lapping and licking inside him as he moaned, seeming to enjoy it just as much as Ben did. 

Eventually, Hux slipped a finger in alongside his tongue, shoving past the ring of muscles which clenched down tightly at the intrusion. He didn’t bother with platitudes this time, just grunt and pushed harder until Ben relented and he managed to bury his finger to the second knuckle. Admittedly, it stung, and Ben whimpered and bit at his lip. Hux continued licking him as his finger searched deeper, pressing in and out in slow and deliberate motions. 

Ben was moaning again soon enough. He turned his face out, settling his cheek against the cushion instead, and he watched the curtains flutter just a tough in the slight breeze that had started up outside. Hux’s finger moved faster, pushing all the way inside once more. It had actually been awhile since he’d been fucked, and Ben was reminded of how good having something inside him was. 

The second digit working its way inside him made Ben tense up again. Hux grumbled at him, pulling back enough to bite at his cheek. “Relax.” His voice came in a whisper, but with a commanding tone. Ben did his best to obey. As the finger sunk deeper, he felt his rim stretch, a slight stinging caused, and Ben wished for just a bit of lubrication that wasn’t saliva. However, this was all he could have, and Hux wasn’t stopping. Ben didn’t really want him to stop. 

Once his fingers were buried inside, Hux spread them, scissoring out in opposite directions, and Ben let out a soft screech in surprise. “Ah, ah, ah!” He gripped tighter to the chair, then let his mouth drop open, a series of moans and pained gasps escaping him. It felt good and hurt at the same time, and when Hux bit into his ass again, he actually moaned. The sensations were coming at him all at once, and it was confusing his brain. 

Hux pulled his fingers out slowly, and Ben began to relax. It was silly of him to think there would be a reprieve, however, His hips were grabbed, and Hux pulled him backwards as he stood up, and Ben shuffled down the length of the lounge chair, until his feet hung off the end, and his ass was conveniently placed. Hux pushed his head down against the cushion, making it obvious what he preferred. 

“You’ve been a good boy. Now let’s see what this tight ass feels like.” He hooked two fingers into Ben’s hole again, leaning in and spitting. Ben felt the saliva sliding deep inside him. The fingers vanished, and only a moment later, Hux’s cock pressed against his rim. “Fuck yeah,” he said, putting just the tip him and giving small presses to test if Ben could accomodate him. 

Ben bit his lip, burying his face into the cushion again. Even the tip felt like too much, but he worked to make himself relax. Soon, more was being fed into him. Hux cursed under his breath, smacking Ben’s ass, and he pushed deeper. For a long stretch, his cock was in just past the tip, and Hux gave shallow, meaningless thrusts. 

Until he grew impatient and slammed in all the way. Ben felt the blinding pain first, his ass forced to stretch enough, a fire shooting straight through his ass, and he felt Hux’s balls resting against his ass. Hux gripped at his cheeks, massaging and stroking. The pain didn’t last, fading out as Hux reached around him to give his cock a solid stroke. Ben melted into the chair and Hux began to fuck him. 

He didn’t start off slow and build up. Hux’s cock began pistoning inside him, moving quick enough that Ben couldn’t keep track of him. He simply moaned and let his arm drop off the side of the chair, knuckles scraping along the ground as his body rocked back and forth. When arousal began pooling in his gut, a heaviness, it had only been a minute. Ben came before Hux even hit his sweet spot, splattering semen down on the chair under him. 

Hux didn’t even slow. “Oh, did you come already?” he asked, a teasing but breathless voice. He gripped Ben’s hips and controlled the angle, and soon Ben could see stars as his prostate was hit with blinding accuracy. It left Ben to think Hux had been purposefully avoiding it this whole time. Not even over the crest of his first orgasm, Ben could already feel another growing. It was insanely overwhelming, the desire coursing under his flesh. Hux pounding him from behind led to him calling out for another release. 

“Make me come, sir! Make me come, please!” 

Hux grunted in recognition of his words, and he began thrusting harder and harder, until Ben felt like he could pop. His cock dribbled more cum as his second orgasm hit him, seemingly not even five minutes later, and Hux emptied a load inside him. 

The fucking came to an end, and Hux pulled out, taking a side step to the other chair and sitting down. Ben slumped to the side, his knees falling out from under him, unable to support him anymore. His legs hung off the chair and semen dripped down his leg. Hux panted, wiping his brow and neck, then fanning himself. The muggy heat didn’t leave the cabana unaffected. 

“That was good,” he said, casually, as if they’d just had dinner. Ben gaped at him, breathing heavily and unable to speak. Hux grinned at him smugly, then he stood up and reached over to smack Ben’s ass. “For a first timer, you impressed me. Well, I hope I see you tomorrow night,” he said, then began gathering his clothes and putting them back on. Ben still hadn’t moved. The arousal was wearing away. His ass hurt. 

“If you’re here tomorrow, and you let me have you again, I’ll double the money,” he said, coming and crouching down by Ben’s face, smoothing some hair away from his sweaty cheeks. “That sound alright to you?” 

“S-sure,” Ben said, breathless still. 

“Alright.” He patted his cheek gently, then stood up. “Clean this up before you go.” The curtain opened, and Hux left, letting it fall back into place. Ben listened to his footsteps heading away before he sat up. 

Wincing, he kicked off his heels, not even willing to try to walk in them. Standing up, he pulled his panties up, then turned around to look at the cum on the chair. It was drying on his leg as well, but he could worry about that later. His lipstick was also smeared on the white cushions, and he let out a soft groan at that. Limping, he went to grab some cleaning supplies. Worst job ever, he thought, as he walked barefoot down the sidewalk, back to the cabana, spray bottle and sponge in hand. 

Pausing, he reached behind him and made sure his skirt was pulled back down to cover his ass, and he blushed a bit. Perhaps, it was the best job ever at the same time. 


End file.
